Sodium Azide → Azidomethyl 2,2-dimethylpropanoate

HRID 450475Notes

Reaction equation

HRID 450475 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[C:5]([O:11][CH2:12]Cl)(=[O:10])[C:6]([CH3:9])([CH3:8])[CH3:7]>O.CCOC(C)=O>[C:5]([O:11][CH2:12][N:1]=[N+:2]=[N-:3])(=[O:10])[C:6]([CH3:9])([CH3:8])[CH3:7]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 87885Chloromethyl pivalate

Product 1

HCID 11521126Azidomethyl 2,2-dimethylpropanoateYield 64%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

Sodium azide (1.942 g, 29.9 mmol) was added to a suspension of chloromethyl pivalate (3.00 g, 19.92 mmol) in water (5 mL) and stirred vigorously at 90° C. for 16 h. The reaction mixture was diluted with water (20 mL) and EtOAc (20 ml). The organic layer was washed with brine, dried (Na2SO4) and concentrated to afford azidomethyl pivalate as a liquid (2 g, 64% yield). 1H NMR (400 MHz, Acetone-d6): δ 5.23 (s, 2H), 1.22 (s, 9H).

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-261972adfabb49d5ac948402e879cdfb
Source dataset
uspto-grants-2013_07
Patent number
US08486951B2

Reaction notes

Loading…